Abstract
Marine algae from the genus Karlodinium are known to be involved in fish-killing events worldwide. Here we report for the first time the chemistry and bioactivity of a natural product from the newly described mixotrophic
dinoflagellate Karlodinium armiger. Our work describes the isolation and structural characterization of a new polyhydroxypolyene named karmitoxin. The structure elucidation work was facilitated by use of 13C enrichment and high-field 2D NMR spectroscopy, where 1H−13C long-range correlations turned out to be very informative. Karmitoxin is structurally related to amphidinols and karlotoxins; however it differs by containing the longest carbon−carbon backbone discovered for this class of compounds, as well as a primary amino group.
Karmitoxin showed potent nanomolar cytotoxic activity in an RTgill-W1 cell assay as well as rapid immobilization and eventual
mortality of the copepod Acartia tonsa, a natural grazer of K. armiger.
dinoflagellate Karlodinium armiger. Our work describes the isolation and structural characterization of a new polyhydroxypolyene named karmitoxin. The structure elucidation work was facilitated by use of 13C enrichment and high-field 2D NMR spectroscopy, where 1H−13C long-range correlations turned out to be very informative. Karmitoxin is structurally related to amphidinols and karlotoxins; however it differs by containing the longest carbon−carbon backbone discovered for this class of compounds, as well as a primary amino group.
Karmitoxin showed potent nanomolar cytotoxic activity in an RTgill-W1 cell assay as well as rapid immobilization and eventual
mortality of the copepod Acartia tonsa, a natural grazer of K. armiger.
| Originalsprog | Engelsk |
|---|---|
| Tidsskrift | Journal of Natural Products |
| Vol/bind | 80 |
| Udgave nummer | 5 |
| Sider (fra-til) | 1287−1293 |
| Antal sider | 7 |
| ISSN | 0163-3864 |
| DOI | |
| Status | Udgivet - 26 maj 2017 |
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